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Check prices for these dates

Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct
In one month
23 Oct - 25 Oct
In two months
20 Nov - 22 Nov

Our top choices for Southwest Side bed & breakfast

A modern living room with a sofa, a coffee table, and a dining area with a table and chairs.

1. Dorothy's

Dorothy's
2.0 star property
Lakeview
8.6 out of 10, Excellent, (184 reviews)
"Space was so clean and modern. Breakfast was good also. Very nice stay."
United States
Steven
The price is 1.491.941 ₫
2.661.110 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Dorothy's
A bathroom with a glass-tiled wall, a sink, and a shower area.

2. Ray's Bucktown B&B

Ray's Bucktown B&B
3.5 star property
Bucktown
9.8 out of 10, Exceptional, (415 reviews)
"Superb breakfast and very friendly staff. Great place to stay!"
United States
mary
The price is 4.801.420 ₫
5.420.220 ₫ total
includes taxes & fees
28 Sept - 29 Sept
Ray's Bucktown B&B
A spacious kitchen with white cabinetry, a central island with bar stools, pendant lighting, and a large window with a view.

3. The Sono Chicago

The Sono Chicago
3.5 star property
Near North Side
10.0 out of 10, Exceptional, (557 reviews)
"It was a very comfortable hotel. We loved the free street parking, easy access to public transportation, coffee, breakfast, bottled water, bubbly water and snacks. I will stay here again!"
United States
Christie
The price is 5.876.000 ₫
6.897.800 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Sono Chicago
A fire pit surrounded by glass pebbles, with a television displaying a football game in the background.

4. The Villa Toscana

The Villa Toscana
2.5 star property
Lakeview
8.0 out of 10, Very good, (675 reviews)
"Was a nice house the room we stayed in was cozy bed was really comfortable and in walking distance to wrigley field would definitely stay here again"
United States
John
The price is 1.972.792 ₫
3.355.541 ₫ total
includes taxes & fees
26 Oct - 27 Oct
The Villa Toscana
A modern living room with leather sofas, a dining area, and large windows offering a view of greenery.

5. House 5863 - Chicago Bed and Breakfast

House 5863 - Chicago Bed and Breakfast
3.5 star property
Edgewater
9.2 out of 10, Wonderful, (519 reviews)
"good"
United States
jiantao
The price is 3.274.992 ₫
5.448.183 ₫ total
includes taxes & fees
4 Oct - 5 Oct
House 5863 - Chicago Bed and Breakfast
A well-lit hallway with a wooden dresser, a table with chairs, and a blue patterned rug.

6. Harvey House Bed & Breakfast

Harvey House Bed & Breakfast
4.0 star property
Oak Park
9.8 out of 10, Exceptional, (135 reviews)
"We had a comfortable stay. Bed was great, host was very accommodating and location was great!"
United States
Monica
The price is 7.607.339 ₫
8.442.722 ₫ total
includes taxes & fees
6 Oct - 7 Oct
Harvey House Bed & Breakfast
A wooden staircase with built-in seating and potted plants, leading to a modern interior with large windows and a mezzanine level.

7. The Publishing House B&B

The Publishing House B&B
3.5 star property
Downtown Chicago
9.8 out of 10, Exceptional, (217 reviews)
"The best hotel breakfast I have ever had. I will return for the breakfast!"
United States
Kathryn
The price is 6.458.752 ₫
7.291.285 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Publishing House B&B
A grand foyer with a wooden staircase, a chandelier, and a large window.

8. Villa D' Citta

Villa D' Citta
3.5 star property
Lincoln Park
9.4 out of 10, Exceptional, (125 reviews)
"What a pleasant stay, staff was welcoming and wanting to make sure our needs were met with our expectations. Meals were abundant and homemade. Rooms w/bath were clean with abundant towels. We will stay again."
United States
Jeffrey
The price is 6.546.085 ₫
7.684.535 ₫ total
includes taxes & fees
7 Oct - 8 Oct
Villa D' Citta
A brick building with a sign for The Wicker Park Inn, including a phone number and website.

9. Wicker Park Inn

Wicker Park Inn
3.5 star property
West Town
9.0 out of 10, Wonderful, (283 reviews)
"Great location. Staff was very helpful.👍"
United States
Michael
The price is 7.676.997 ₫
9.011.686 ₫ total
includes taxes & fees
26 Oct - 27 Oct
Wicker Park Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Southwest Side Hotel Reviews

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Great location, away from the bustle, but close enough. Overall a good stay"
Mahesh 2-night trip
Posted less than an hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Southwest Side

Southwest Side B&B information

Number of reviews
2,428
Accommodation
9 B&B
Lowest Price
2.661.110 ₫
Highest Price
9.011.686 ₫